Who's the Boss?

Dear Chuck and Garland: I am so happy I ran across your blog! I'm really do need some advice from a black man's perspective.

Two years ago I met a nice guy at work. He was my boss, although he worked in another location and we saw each other in person only once a week or so. During this time I was living with my then-boyfriend and was being harassed by another employee. My boss became a sounding board for my work problems and I developed a crush on him. I didn't say anything to him out of respect for my then-boyfriend and because I believe that type of office romance is a no-no.

About six months ago I broke up with my boyfriend and moved into my own place. My boss and I have moved on to other jobs. Should I tell this guy that I like him? And if so, how? We only talk and/or email about once a month, so I don't feel comfortable calling asking him out for drinks (a friend's suggestion) or boldly saying "Gat-dayum I want you!" (another friend's suggestion). I'm also embarrassed because I had a hard time dealing with the enormous amount of stress at our previous job. The past six months-year have made me grow tremendously, but I'm not sure that he knows that. I'm not looking for a relationship, even though it would be nice.

My main desire is to get to know him better and at least be his friend so I can see if my feelings for him are genuine or just the result of the situation we were both in when we met. He's only three years older than me, so there are no daddy/authority figure issues going on here. Part of me thinks he would've said something already if the attraction was mutual. He knows I'm single, so is it possible that he's just not into me? Should I say something?

Signed, 30 yet feeling like a shy (dumb?) teenager

CHUCK: 30 Yet, thanks for the question. There is only one way that you're going to find out whether this former supervisor shares your feelings, and that is to just approach him.

I have had a number of workplace relationships in the past. They have never been with a supervisor, but they have also never had the distance that you have now. I can say that if the parties are mature, it can be a worthwhile experience. The fact that you are no longer in the same workplace removes one major obstacle. I think that your main obstacle here is that you are apprehensive about him still knowing things about you from your shared past. Unfortunately, you can't count on him to forget, or un-know things that you already know. So the best way to deal with this situation is to approach it straight.

Before you do that, though the way to deal with him, is to let him know that that situations between you have changed. You say that you have grown more mature. The best method to convey that message is, as your friend says, to ask him out. That way, you can show him, and not tell him that the issues you may have had when you worked together, are now gone.

Rather than laying all your cards on the table right then, you should observe him and see whether any interest exists. Supervisors, those with common sense, at least, should try to restrain any personal attractions that they have for their employees, so as to stay out of court. Maybe he still looks at you that way. Maybe not.

Don't obsess over why he hasn't tried to make the first move. For a supervisor who counseled an employee through a harassment situation to, a couple years later, ask that employee for a date... Well, you see, it just doesn't sound right. He may feel that dealing you dealing with him could bring up memories and associations you might want to avoid. You, however, aren't constrained by such propriety. And if you feel like getting to know this guy better, you should.

GARLAND: Thanks for this question - its a very good one and very special to me personally. When my wife and I first met, it was her that made the initial contact, and had she not - we may not be happily married today. SO DEFINITELY REACH OUT TO HIM!

Like Chuck said, don't stress over the fact that he hasn't reached out to YOU yet. He may have some left over "boss" barriers up and doesn't want to put you in an uncomfortable position. OR - he may have the same question in a que on "What Are Women Thinking?"

For me, LUNCH has always been the safest way to gauge a person. Dinner or Evening Drinks involves meeting at someones house, or picking someone up, or getting a sitter, or dressing up, and maybe dancing and crowds and then there's the whole kiss-goodnight drama. Breakfast is cute, but not practical. LUNCH is what I suggest to you.

If you can find out where he works - try to find a reason to be up that way at a store or a meeting or something, then call him a few days prior and say something like, "Hey Kevin, how's it going. I'm going be near your office one day next week and wanted to know if you wanted to grab some lunch..." Make sure you don't say a specific day at first, because if he can't make it on the day you say, then you've over played your hand and it might not look so nonchalant. Let him say what day is good for him and thne go from there. Lay back and enjoy yourself. It sounds like you have a great attitude about the whole thing - just let whatever happen.

Best of luck to you! Let us know how things play out.